Hydroxyamides versus amino alcohols in the enantioselective addition of diethylzinc to benzaldehyde

Tetrahedron Asymmetry

Volumn 19, Issue 17, 2008, Pages 2003-2006

  de las Casas Engel, Tomás ^a   Maroto, Beatriz Lora ^a   Martínez, Antonio García ^a   de la Moya Cerero, Santiago ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

10 AMINO 10 OXOISOBORNEOL DERIVATIVE; 10 AMINO OXOISOBORNEOL DERIVATIVE; AMIDE; BENZALDEHYDE; BORNEOL; DIETHYLZINC; HYDROXYAMIDE DERIVATIVE; ISOBORNEOL DERIVATIVE; KETOPINIC ACID; TITANIUM; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHELATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHIRALITY; COORDINATION; ENANTIOMER; ENANTIOSELECTIVITY; LIGAND BINDING; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PRODUCT RECOVERY; STRUCTURE ACTIVITY RELATION;

EID: 51449115884     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.08.008     Document Type: Article

References (43)

1. Soai K., and Niwa S. Chem. Rev. 92 (1992) 833
2. Pu L., and Yu H.H.L. Chem. Rev. 101 (2001) 767
3. In: Ojima I. (Ed). Catalytic Asymmetric Synthesis (2000), Wiley-VCH, New York
4. In: Mikami K., and Lautens M. (Eds). New Frontiers in Asymmetric Catalysis (2007), Wiley-Interscience, Hoboken
5. Pu L. Tetrahedron 59 (2003) 9873
6. Lu G., Li Y.-M., Li X.-S., and Chan A.S.C. Coord. Chem. Rev. 249 (2005) 1736
7. Most organozinc reagents can be easily prepared and stored, and are compatible with many functional groups:. Knochel P. In: Beller M., and Bolm C. (Eds). Transition Metals for Organic Synthesis (1998), Wiley-VCH, Weinheim
8. Frantz D.E., Fässler R., Tomooka C.S., and Carreira E.M. Acc. Chem. Res. 33 (2000) 373
9. For example: In drug synthesis: Kanai, M.; Ishii, A.; Kuriyama, M.; Yasumoto, M.; Inomiya, N.; Otsuka, T.; Ueda, H. Patent written in Japanese. Patent No. JP 2003226659.
10. In liquid-crystal preparation: Armstrong, J. D.; McWilliams, J. C. U.S. Patent 5,977,371.
11. Only certain chiral hydroxysulfonamides are efficient ligands for the enantioselective addition of organozinc reagents to ketones:. García C., LaRochelle L.K., and Walsh P.J. J. Am. Chem. Soc. 124 (2002) 10970
12. Yus M., Ramón D.J., and Prieto O. Tetrahedron: Asymmetry 13 (2002) 21
13. Ramón D.J., and Yus M. Chem. Rev. 106 (2006) 2126
14. Fang T., Du D.-M., Lu S.-F., and Xu. J. Org. Lett 7 (2005) 2081
15. Blay G., Fernández I., Marco-Aleixandre A., and Pedro J.R. J. Org. Chem. 71 (2006) 6674
16. Testa M.L., Anista L., Mingoia F., and Zaballos-García E. J. Chem. Res. 71 (2006) 6674
17. Blay G., Fernández I., Marco-Aleixandre A., and Pedro J.R. J. Org. Chem. 71 (2006) 6674
18. Blay G., Fernández I., Marco-Aleixandre A., and Pedro J.R. Synthesis (2007) 3745
19. Blay G., Fernández I., Hernández-Olmos V., Marco-Aleixandre A., and Pedro J.R. J. Mol. Catal. A: Chem. 276 (2007) 235
20. de las Casas Engel T., Lora Maroto B., García Martínez A., and de la Moya Cerero S. Tetrahedron: Asymmetry 19 (2008) 646
21. Some exceptions are reported in Refs.5d,5e,5g
22. Mainly on the basis of the vast work carried out by Noyori in this area. For example, see:. Kitamura M., Suga S., Kawai K., and Noyori R. J. Am. Chem. Soc. 108 (1986) 6071
23. Kitamura M., Okada S., Soga S., and Noyori R. J. Am. Chem. Soc. 111 (1989) 4028
24. Yamakawa M., and Noyori R. J. Am. Chem. Soc. 117 (1995) 6327
25. Yamakawa M., and Noyori R. Organometallics 18 (1999) 128
26. A seminal and unique comparison study for the catalytic activity of one hydroxyamide and its corresponding amino alcohol was reported by Oppolzer in 1988, demonstrating a higher activity of the latter for the enantioselective addition of diethylzinc to benzaldehyde:. Oppolzer W., and Radinov R.H. Tetrahedron Lett. 29 (1988) 5645
27. 2-Symmetric ligands are considered advantageous because they can reduce to the half the number of possible transition states in enantioselective reactions:. Whitesell J. Chem. Res. 89 (1989) 1581
28. Halm C., and Kurth M.J. Angew. Chem., Int. Ed. 37 (1998) 510
29. 3 symmetry in asymmetric catalysis and chiral recognition, see:. Moberg C. Angew. Chem., Int. Ed. 37 (1998) 248
30. Gibson S.E., and Castaldi M.P. Angew. Chem., Int. Ed. 45 (2006) 4718
31. As example for the importance of the ligand́s conformational flexibility see:. García Martínez A., Teso Vilar E., García Fraile A., de la Moya Cerero S., and Lora Maroto B. Tetrahedron 61 (2005) 3055
32. García Martínez A., Teso Vilar E., García Fraile A., de la Moya Cerero S., Martínez Ruiz P., and Díaz Morillo C. Tetrahedron: Asymmetry 18 (2007) 742
33. 12) yielded the resulting enantioenriched mixture of 1-phenylpropan-1-ol. The ee was determined by chiral GC (cyclodex-B). The dominant configuration was determined by both the sign of the mixture's specific rotation and the elution time in chiral GC.
34. de las Casas Engel T., Lora Maroto B., García Martínez A., and de la Moya Cerero S. Tetrahedron: Asymmetry 19 (2008) 269
35. Hari Y., and Aoyama T. Synthesis 4 (2005) 583
36. 2: 266.1994).
37. 6: 627.4247).
38. 2: 390.3246).
39. Characterization data agree with those previously reported by Aoyama (Ref. 13).
40. +: 586.1712).
41. Amidation was performed by standard activation with N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride/DMPA (yields: 84-98%).
42. Oppolzer W., and Radinov R.N. Tetrahedron Lett. 29 (1988) 5645
43. 2) for 7)